US2629697A - Alkyl aryl sulfonate-liquid hydrocarbon-aliphatic hydroxy compound compositions - Google Patents

Alkyl aryl sulfonate-liquid hydrocarbon-aliphatic hydroxy compound compositions Download PDF

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US2629697A
US2629697A US54568A US5456848A US2629697A US 2629697 A US2629697 A US 2629697A US 54568 A US54568 A US 54568A US 5456848 A US5456848 A US 5456848A US 2629697 A US2629697 A US 2629697A
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water
sodium
monobutyl ether
hydroxy compound
aliphatic hydroxy
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US54568A
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William K Langdon
Earl F Soop
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Wyandotte Chemicals Corp
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Wyandotte Chemicals Corp
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

Definitions

  • This. invention relates to a novel, and highlt useful, liquid composition based essentially upon the ingredients: sodium alkyl aryl sulfonate, liquid hydrocarbon and an aliphatic hydroxy compound. More particularly, the sodium alkyl aryl sulfonate ingredient of our invention is sodium kerylbenzenesulfonate 1 containing not over 30% by weight Na2so4; and the liquid hydrocarbon is a petroleum distillate of the kerosene type. Mixtures of sodium kerylbenzenesulfonate and a petroleum distillate hydrocarbon boiling in the kerosene range (l50-300 C. at atmospheric pressure) form extremely viscous, gelled or wax-like masses which are of an opaque appearance.
  • composition of our invention is therefore of value as a base product in the formulation of printing inks, paints and liquid dry cleaning compositions wherein it is sought to obtain the advantages of a surface active or wetting agent such as sodium kerylbenzenesulfonate in the presence of a liquid hydrocarbon.
  • Our invention also includes a single phase liquid type composition, wherein water is added .to the base composition first mentioned above.
  • water is added .to the base composition first mentioned above.
  • Such single phase, liquid mass compositions of our invention are particularlyuseful as emulsion type cleaning compounds for removing oil, dirt and soil from metal surfaces.
  • the working solutions, or more accurately speaking, the working suspensionsor emulsions of such single phase liquid compositions consist of approximately 1 part of liquid composition to 100 parts of water. They are also useful as base compositions in which additional detergent ingredients, such as organic solvents, water softening compounds, soil Application October 14, 1948, Serial No. 54,568
  • Sodium kerylbenzenesulfonate is an excellent surface active agent and detergent when employed in aqueous solutions.
  • a lyophilic, oil-dissolving hydrocarbon such as a petroleum distillate
  • Aqueous solutions of sodium kerylbenzenesulfonate however are immiscible with such liquid hydrocarbons; even though aqueous solutions of higher alkyl aryl sulfonates, whose alkyl group contains 20-30 carbon atoms and is derived from a white oil or liquid paraflin boiling in the range of 195-295 C. at 15 mm. pres.- sure are miscible with white oil and Stoddard solvent (cf. U. S. Patent 2,317,986).
  • sodium kerylbenzenesulfonate and the liquid hydrocarbon form nearly solid waxlike mixtures.
  • a wax-like, opaque and highly viscous mixture of kerylbenzenesulfonate and a normally liquid petroleum distillate hydrocarbon boiling in the kerosene range can be converted to a clear, fluid mass through the medium of a coupling agent consisting of an aliphatic hydroxy compound having 4 to 10 carbon atoms and selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, mono(n-)butyl ether of ethylene glycol, mono(n)butyl ether of di-ethylene glycol, mono(n-)butyl ether of propylene glycol and 2-ethylhexanediol-L3.
  • a coupling agent consisting of an aliphatic hydroxy compound having 4 to 10 carbon atoms and selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, mono(n-)butyl ether of ethylene glycol, mono(n)butyl ether of di-ethylene glycol, mono(n
  • a sodium kerylbenzenesulfonate of at least"70% active agent content (1. e. containing not over 30% of NazSOr) is employed,
  • Example 5 The formulation of Example 5 was found" to be particularly excellent in that it was capable of being subjected to extremely low temperature TABLE 111 Son 1' A m synonym Trade fili l" i p mg ge Name e) i ppearance Propyl Alcohol iso-Propanol .4 Clear, but split. Tetradecvl Alcohol n-Tetradecanol 4 Opaque, stifi. Mfilzfi-Ethyl Ethylene Glycol Ethyl Gellosolve- 4 Do.
  • Example 5 Kerosene 55 Sodium kerylbenzenesulfonate (30% NazSOai) 24 Water 18 Amyl alcohol (Pentasol) 3 conditions (i. e., frozen with solid carbon dioxide), such as might be encountered under certain storage conditions, and on being restored to the liquid state by warming to room temperature, retained its single phase character.
  • Penasol Water 18 Amyl alcohol
  • a single phase, non-viscous, fluid composition consisting essentially of 55-71% by weight of a normally liquid petroleum distillate hydrocarbon boiling in the kerosene range, 12-20% of a sodium kerylbenzenesulfonate of not over 30% Na2SO4 content and whose keryl group contains 9-16 carbon atoms; 15-25% water; and 2-4% of an aliphatic hydroxy compound selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, monobutyl ether of ethylene glycol, monobutyl ether of diethylene glycol, monobutyl ether of propylene glycol and 2-ethylhexanediol-L3.
  • An emulsion forming composition consisting essentially of 55-71% by weight of kerosene, 12-20% of sodium kerylbenzenesulfonate of not over 30% Na2SO4 content and whose keryl group contains 9-16 carbon atoms, 15-25% of water and 2-4% of an aliphatic hydroxy compound selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, monobutyl ether of ethylene glycol, monobutyl ether of di-ethylene glycol, monobutyl ether of propylene glycol and 2-ethylhexanediol-1,3.
  • a clear, single phase liquid composition consisting of approximately 63% by weight of kerosene, 20% of sodium kerylbenzenesulfonate of not ever 30% Na2SO4 content and whose keryl group contains 9-16 carbon atoms, 15% of water and 2% of monobutyl ether of ethylene glycol.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Description

Patented Feb. 24, 1953 UNITED STATES ALKYL ARYL SULFONATE-LIQUID HYDRO- CARBON -ALIPHATIC HYDROXY COM- POUND GOMPOSITIONS William K. Langdon and Earl F. Soop, Grosse Ile,
Mich., assignors to Wyandotte Chemicals Corporation, Wyandotte, Mich., a corporation of Michigan 1 No Drawing.
. 1 This. invention relates to a novel, and highlt useful, liquid composition based essentially upon the ingredients: sodium alkyl aryl sulfonate, liquid hydrocarbon and an aliphatic hydroxy compound. More particularly, the sodium alkyl aryl sulfonate ingredient of our invention is sodium kerylbenzenesulfonate 1 containing not over 30% by weight Na2so4; and the liquid hydrocarbon is a petroleum distillate of the kerosene type. Mixtures of sodium kerylbenzenesulfonate and a petroleum distillate hydrocarbon boiling in the kerosene range (l50-300 C. at atmospheric pressure) form extremely viscous, gelled or wax-like masses which are of an opaque appearance.
. However, according to our invention, when an aliphatic hydroxy compound is added to a mixture of 1 part by weight of kerosene, and /6- part of sodium kerylbenzenesulfonate in amounts as little as 2% by weight (all parts and percentages hereinafter given are by weight, unless otherwise stated), the mass promptly loses its vis- .cous character, becomes very fluid and becomes transparent to translucent in appearance. The composition of our invention is therefore of value as a base product in the formulation of printing inks, paints and liquid dry cleaning compositions wherein it is sought to obtain the advantages of a surface active or wetting agent such as sodium kerylbenzenesulfonate in the presence of a liquid hydrocarbon.
Our invention also includes a single phase liquid type composition, wherein water is added .to the base composition first mentioned above. "We'ha've' discovered that the aliphatic hydroxy compound coupling agent renders it possible to introduce water into the composition and still maintain a clear, translucent-to-transparent, single phase liquid mass.
Such single phase, liquid mass compositions of our invention are particularlyuseful as emulsion type cleaning compounds for removing oil, dirt and soil from metal surfaces. The working solutions, or more accurately speaking, the working suspensionsor emulsions of such single phase liquid compositions consist of approximately 1 part of liquid composition to 100 parts of water. They are also useful as base compositions in which additional detergent ingredients, such as organic solvents, water softening compounds, soil Application October 14, 1948, Serial No. 54,568
6 Claims. (Cl. 252-161) retention agents, alkaline salts, etc. may be incorporated.
Sodium kerylbenzenesulfonateis an excellent surface active agent and detergent when employed in aqueous solutions. In the formulation of an emulsion type cleaner a lyophilic, oil-dissolving hydrocarbon, such as a petroleum distillate, is desirable. Aqueous solutions of sodium kerylbenzenesulfonate however are immiscible with such liquid hydrocarbons; even though aqueous solutions of higher alkyl aryl sulfonates, whose alkyl group contains 20-30 carbon atoms and is derived from a white oil or liquid paraflin boiling in the range of 195-295 C. at 15 mm. pres.- sure are miscible with white oil and Stoddard solvent (cf. U. S. Patent 2,317,986). And as mentioned above, sodium kerylbenzenesulfonate and the liquid hydrocarbon form nearly solid waxlike mixtures.
We have discovered that first of all, a wax-like, opaque and highly viscous mixture of kerylbenzenesulfonate and a normally liquid petroleum distillate hydrocarbon boiling in the kerosene range can be converted to a clear, fluid mass through the medium of a coupling agent consisting of an aliphatic hydroxy compound having 4 to 10 carbon atoms and selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, mono(n-)butyl ether of ethylene glycol, mono(n)butyl ether of di-ethylene glycol, mono(n-)butyl ether of propylene glycol and 2-ethylhexanediol-L3.
Secondly, we have discovered that the foregoing resultant clear, fluid mass of sodium kerylbenzenesulfonate, petroleum distillate hydrocarbon and coupling agent is compatible with water. By the addition of critical amounts of water as hereinafter described in detail, the clear, fluid appearance of the mixture is undisturbed. Such a clear, single phase mixture can then be most readily dispersed in a relatively large volume of water, to make up the emulsion type cleaning solution or suspension, previously mentioned.
We have also discovered that the ratio of the ingredients, in order to obtain a clear, single phase mixture, must be maintained within the following stated critical ranges:
Ingredient: Per cent by weight Petroleum -71 Sodium kerylbenzenesulfonate 12-20 Water 15-25 Coupling agent 2-4 The above stated range proportions of ingrediplate.
ents, for convenience in formulating, can be alternatively stated as follows:
Petroleum hydrocarbon 1 part by weight Sodium kerylbenzenesulfonate' part Water M /2 part Coupling agent 24% by Weight of tot-at com-position Sodium kerylbenzenesulfonate in both its saltfree form (i. e. with Na2SO4 extracted) and in its salt-containing or salt-built form, can be em ployed in making the compositions'of our inven-- tion. However we prefer to use, and find that the best results are obtained when a sodium kerylbenzenesulfonate of at least"70% active agent content (1. e. containing not over 30% of NazSOr) is employed,
The following examples will serve to illustrate to those skilled in the art, and in greater detail, the manner in which the principle of our invention. may be practiced.
Example, 1
Sodium kerylbenzenesulfonate of the salt-free type (i e. containing only 0.25% NazSOl) in the amount of 10- grams was stirred with 30 grams of kerosene in a beaker, while warming on a hot A gradual swelling of the sodium kerylbenzenesulfonate occurred, until a Viscous, nonp'our'able, translucent wax-like mass was formed. Amyl alcohol (commercial grade of mixed amyl alcohols sold under the trade name Pentasol) in the amount of 1 cc. or 0.8 gram (2% by Weight) was then added. After stirring for a short time, the viscosity of the mixture was substantially reduced, so that the resultant mixture was quite fluid. On adding water (approximately 15 cc.) to the mixture, a clear transparent solution was obtained. This solution formed a stable, milky emulsion when added to a large volume of water.
Example .2
Sodium kerylbenzenesulfonate containing 70% activeagent (i. e. about 30% by weight NazSOr) in the amount of 20 grams wasmixed with 60 grams of kerosene and allowed to stand for two hours. To 60 grams of this mixture, water was added in 1 ml. increments and with vigorous agitation. After the addition of 2 ml.v of water the mixture thickened and progressively became thicker until a total of 9 ml. of water had been added. The'mixture was then slightly warmed, more ml. of water added, followed by the addition of 1 cc. or 0.9 gram of monobutyl ether of ethylene glycol (commercial grade available TABLE 1 Sodium Mono- Kerylbenbutyl Kerosene Water zene Sulion--. IEth er of Results etc (30% Ethylene Na SOO Glycol L 3 '24. 0 18 14 2. 3 Clear, fluid. 54.9 23.8 18.3 3.0 Neatlyc'leaniluid. 54. 6 23. 6 18. 2 3. 6 Do. 54-. 3 2'3. 4 18.1 4. 2" Split into 2181mm. 53. 9 23. 2 18. 0 4. 9 5 Do.
The foregoing 24% critical rangecontent of monobutyl ether of ethylene glycol. is equally well applicable to the other selected coupling agents within the scope of our'invention.
We are unable to evolve any chemical or scientific theory of why the particular aliphatic hydroxy compounds selected should be operable for the purposes of our invention. Several homologous .oxy-- and hydroxy-aliphatic. compounds were added to a base mixture consistingof 3 grams of sodium kerylbenzenesulfonate (containing 30% N'a2SO4), S-grams of kerosene and 2.8 cc. of water. The addition was made in uniform 0.4 cc. amounts of'the oxyor hydroxyaliphatic compound. Dependent upon the specific gravity of the oxyor hydroxy-aliphatic compounds tested, this represented 21-23% by weight of the total composition. Accordingly, the test compositions conformed closely to the following formulation:
Couplin agent. 2
Listed in Table II below, are those particular aliphatic hydroxy compounds which were found to be operable as coupling agents, according to this test:
TABLE II S on orl Amount I Coupling Agent yn {1 fade Adtgd Appearance Butyl Alcohol.-- n-Butanol 4 0' Amyl Alcohol. Pentasol" 4' flog n-Hexanol. .4 Do. .n-Octanol .4 Do. Decvl Alcohol l l Decanol T D0- n-Butyl araeaeareas13: Repeating: :4 5 53??? fluid gigyl Di-Ethylene Glycol ButylC-arbit'ol"- .4 Neanycleanfluid. er. z-Ethylhexanediol'lfi. --l..-- .4 T n n-Butyl Propylene Glycol Ether" .4 N21??? 3538?, l l i g:
On the other hand, listed below in Table III are those oxyor hydroxy-aliphatic compounds which were not operable:
The formulation of Example 5 was found" to be particularly excellent in that it was capable of being subjected to extremely low temperature TABLE 111 Son 1' A m synonym Trade fili l" i p mg ge Name e) i ppearance Propyl Alcohol iso-Propanol .4 Clear, but split. Tetradecvl Alcohol n-Tetradecanol 4 Opaque, stifi. Mfilzfi-Ethyl Ethylene Glycol Ethyl Gellosolve- 4 Do.
er. Di-Ethyl Ethylene Glycol Ether- "Di-Ethyl Cellos0lve.- 4 Do. Mono-Methyl Di-Ethylene Gly- "Methyl Carbitol 4 Do.
col Ether.
Diacetone Diacetone Alcohol 4 Opaque, slightly stiff. Dnnethyl Dloxane Di-Propylene Oxide .4 Clear. stifi. Pentanediol-1,5- Amylene Glycol..- 4 Opaque, stifi. Triethanolamine L 4 Do.
The critical range proportions of ingredients as first hereinbefore stated, are further substantiated and illustrated by the following test results. A base formulation was made up as follows:
Percent Kerosene '7 2.4 Sodium k e r y lb e n z e n e sulfonate (30% NazSOr) 12.0
Water 15.6
Varying amounts of coupling agent were then added to this base formulation so that the resultant test range formulation was substantially as follows: Percent Kerosene 71 As further examples of formulations embodying the principle of our invention, and those which are particularly well suited for commercial purposes as a base mixture for the making up of emulsion type cleaning solutions, we specify th following:
' Example 3 Percent Kerosene 63 Sodium 'k e r y 1b e n z e n e sulfonate (30% Na2SO4) 0 Water 15 Monobutyl ether of ethylene glycol (Butyl Cellosolve) 2 Example 4 Kerosene 60 Sodium kerylbenzenesulfonate (30% N a2S04) 20 Water 18 2-ethylhexanediol-1,3 2
Example 5 Kerosene 55 Sodium kerylbenzenesulfonate (30% NazSOai) 24 Water 18 Amyl alcohol (Pentasol) 3 conditions (i. e., frozen with solid carbon dioxide), such as might be encountered under certain storage conditions, and on being restored to the liquid state by warming to room temperature, retained its single phase character.
Equivalent modes of practicing our invention may be followed provided that they are within the scope and purview of the appended claims.
We, therefore, distinctly claim and particularly point out as our invention:
1. A single phase, non-viscous, fluid composition consisting essentially of 55-71% by weight of a normally liquid petroleum distillate hydrocarbon boiling in the kerosene range, 12-20% of a sodium kerylbenzenesulfonate of not over 30% Na2SO4 content and whose keryl group contains 9-16 carbon atoms; 15-25% water; and 2-4% of an aliphatic hydroxy compound selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, monobutyl ether of ethylene glycol, monobutyl ether of diethylene glycol, monobutyl ether of propylene glycol and 2-ethylhexanediol-L3.
2. A single phase, non-viscous, liquid composition suitable for use as a base product for the make-up of oil-in-water and water-in-oil type emulsions, consisting essentially of a pctroleum distillate liquid hydrocarbon boiling in the kerosene range, /3 part by weight of sodium kerylbenzenesulfonate per part of liquid hydrocarbon; said sodium kerylbenzenesulfohate having not over 30% Na2SO4 content and a keryl group containing 9-16 carbon atoms; A- /2 part of water per part of liquid hydrocarbon; and 24% by weight, total composition basis, of an aliphatic hydroxy compound selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, monobutyl ether of ethylene glycol, monobutyl ether of di-ethylene glycol, monobutyl ether of propylene glycol and 2-ethylhexanedi0l-1,3.
3. An emulsion forming composition consisting essentially of 55-71% by weight of kerosene, 12-20% of sodium kerylbenzenesulfonate of not over 30% Na2SO4 content and whose keryl group contains 9-16 carbon atoms, 15-25% of water and 2-4% of an aliphatic hydroxy compound selected from the group consisting of 4 to 10 carbon atom monohydroxy aliphatic alcohols, monobutyl ether of ethylene glycol, monobutyl ether of di-ethylene glycol, monobutyl ether of propylene glycol and 2-ethylhexanediol-1,3.
4. A clear, single phase liquid composition consisting of approximately 63% by weight of kerosene, 20% of sodium kerylbenzenesulfonate of not ever 30% Na2SO4 content and whose keryl group contains 9-16 carbon atoms, 15% of water and 2% of monobutyl ether of ethylene glycol.
'1 s 5.1 Acleaat sin le.pllerse;liq id. comn sitionicom sisting of; app1:oximately-60% by weight of kero- RE ERENCES, 29%v sodium? kenylbenzenesulfonatel of The following references areof record; in. the
not over 30% NazSOa; content and whose keryl file of this patsnt; group contains 9-16 carbon atoms, 18% of water 5 and. 2 of 2-ethylhexanediol-L3. UNITED STATES PATENTS 6. A clear, single phase liquid composition con- Number lxla-rrieI Date sisting of. approximately 55% by weight of kero- 22 8x107 Schuler Jan. 14, 1941 'sene, 24% of sodium kerylbenzenesulfonate of 2,317,986 Flett May 4, 1943 not over 30% Na2SO4 content and Whose keryl 10 2,356,205 Blair Aug; 22,1944
group contains 9-16 carbon atoms, 18% of'water 09,671 Faust Oct, 22',v 1946 and 3% of amyl alcohol. ,469,378 Flett May 10, 1949 WILLIAM K. LANGDON. 2,531,166 Shaw Nov. 21 1950 EARL F. 8001?.

Claims (1)

1. A SINGLE PHASE, NON-VISCOUS, FLUID COMPOSITION CONSISTING ESSENTIALLY OF 55-71% BY WEIGHT OF A NORMALLY LIQUID PETROLEUM DISTILLATE HYDROCARBON BOILING IN THE KEROSENE RANGE, 12-20% OF A SODIUM KERYLBENZENESULFONATE OF NOT OVER 30% NA2SO4 CONTENT AND WHOSE KERYL GROUP CONTAINS 9-16 CARBON ATOMS; 15-25% WATER; AND 2-4% OF AN ALIPHATIC HYDROXY COMPOUND SELECTED FROM THE GROUP CONSISTING OF 4 TO 10 CARBON ATOM MONOHYDROXY ALIPHATIC ALCOHOLS, MONOBUTYL ETHER OF ETHYLENE GLYCOL, MONOBUTYL ETHER OF DIETHYLENE GLYCOL, MONOBUTYL ETHER OF PROPYLENE GLYCOL AND 2-ETHYLHEXANEDIOL-1,3.
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2978418A (en) * 1956-02-15 1961-04-04 Switzer Brothers Inc Water emulsifiable composition
US2980545A (en) * 1957-10-29 1961-04-18 Dick Co Ab Water base stencil duplicating ink
US3006861A (en) * 1957-10-04 1961-10-31 Gen Dynamics Corp Leak detector fluid
US3024198A (en) * 1958-04-28 1962-03-06 Nopco Chem Co Emulsifier composition
US5281261A (en) * 1990-08-31 1994-01-25 Xerox Corporation Ink compositions containing modified pigment particles
WO1996000759A1 (en) * 1994-06-29 1996-01-11 Creek Simon E A vehicle wash and protectant composition
AU685298B2 (en) * 1994-06-29 1998-01-15 Technacreek Enterprises Pty Ltd A vehicle wash and protectant composition

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2228407A (en) * 1937-04-03 1941-01-14 Stanco Inc Emulsifiable disinfectant
US2317986A (en) * 1940-07-08 1943-05-04 Allied Chemical Dye Corp Composition of matter
US2356205A (en) * 1942-10-21 1944-08-22 Petrolite Corp Process for increasing productivity of subterranean oil-bearing strata
US2409671A (en) * 1943-12-08 1946-10-22 Sonneborn Sons Inc L Substantially oil soluble polyalkyl aromatic sulfonates
US2469378A (en) * 1941-07-28 1949-05-10 Allied Chem & Dye Corp Mixtures of alkyl aryl sulfonates
US2531166A (en) * 1947-11-08 1950-11-21 California Research Corp Detergent concentrate

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2228407A (en) * 1937-04-03 1941-01-14 Stanco Inc Emulsifiable disinfectant
US2317986A (en) * 1940-07-08 1943-05-04 Allied Chemical Dye Corp Composition of matter
US2469378A (en) * 1941-07-28 1949-05-10 Allied Chem & Dye Corp Mixtures of alkyl aryl sulfonates
US2356205A (en) * 1942-10-21 1944-08-22 Petrolite Corp Process for increasing productivity of subterranean oil-bearing strata
US2409671A (en) * 1943-12-08 1946-10-22 Sonneborn Sons Inc L Substantially oil soluble polyalkyl aromatic sulfonates
US2531166A (en) * 1947-11-08 1950-11-21 California Research Corp Detergent concentrate

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2978418A (en) * 1956-02-15 1961-04-04 Switzer Brothers Inc Water emulsifiable composition
US3006861A (en) * 1957-10-04 1961-10-31 Gen Dynamics Corp Leak detector fluid
US2980545A (en) * 1957-10-29 1961-04-18 Dick Co Ab Water base stencil duplicating ink
US3024198A (en) * 1958-04-28 1962-03-06 Nopco Chem Co Emulsifier composition
US5281261A (en) * 1990-08-31 1994-01-25 Xerox Corporation Ink compositions containing modified pigment particles
WO1996000759A1 (en) * 1994-06-29 1996-01-11 Creek Simon E A vehicle wash and protectant composition
AU685298B2 (en) * 1994-06-29 1998-01-15 Technacreek Enterprises Pty Ltd A vehicle wash and protectant composition

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